Castiglion Fiorentino Tuscany villas
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The charm of Tuscany's best holiday villas carefully selected for you

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  • Tuscany villas with private pool, Castiglion Fiorentino
  • Beautiful Tuscan villa with private pool for families and groups
  • Luxury bedroom interior of Tuscany holiday villa
  • Casa Usignoli Tuscan villa for groups of up to 11 with pool
  • View over the pool across the Tuscany countryside near Castiglion Fiorentino

Tuscany Villas & Cottages from Tuscan Charm

Tuscany Villas & Cottages from Tuscan Charm

Easy Cancellation: Cancel 7 Days Before Arrival to Receive a Full Refund

In uncertain times, booking a holiday can be difficult. Now, booking a villa or cottage in Tuscany with us becomes a little easier with our Easy Cancelation Terms: Cancel before 7 days for a full refund. So, if you are planning a family or group holiday to Tuscany, perhaps with a private pool in the Castiglion Fiorentino and Cortona areas, then Tuscan Charm can help.  Whether it be a romantic holiday for two or a family holiday in Tuscany we have something to suit all pockets. We are a co-operative of local villa owners in the Castiglion Fiorentino and Cortona areas of Tuscany, who have provided holiday accommodation to visitors to this region since 1996.  We know and understand how important your holiday is and we plan to make it as perfect as possible. Some villas have a midweek start date for those looking for flexibility or longer stays.

Tuscany and You

Our villas and cottages with swimming pools offer a wonderful opportunity to experience the lifestyle and charm of Tuscany. From a simple Tuscan family cottage to a cosy family villa or a spacious Tuscan family home.  

Our holiday villas are owned and run by English and Italian friends. Our guests are warmly welcomed and we expect you to feel at home the moment you arrive. If you would like us to help with your vacation plans for your family holiday or large group holiday in Tuscany - including toddler-friendly Tuscany cottages - contact us.

Perfect for half term holidays and without any increase in the rates offered. "Tuscany half-term holidays" offer a great family holiday experience and for you to explore the region or to simply relax and enjoy the countryside during an Easter or school half-term break. All bookings for our Tuscany holiday homes come with Easy Cancellation.

Last Minute Tuscany Vacations: Occasionally, we have last-minute weeks available at a special price. If your travel plans are such and you are looking for a great place to stay in Tuscany, please check with us.

Tuscany Villas

Casa Usignoli
  • 11 Sleeps
  • 5 Bedrooms
  • Pool
View Luxury Tuscany villa for up to 11 with 5 bedrooms, private pool and terraces near Castiglion Fiorentino
Casa Peligrini
  • 8 Sleeps
  • 4 Bedrooms
View Tuscany villa with four bedroom and three bathrooms, refurbished with modern kitchen, near Castiglion Fiorentino
Villa Grazia
  • 8 Sleeps
  • 4 Bedrooms
  • Pool
View Tuscany villa for 9 in 4 bedrooms with private pool for families and groups, near Castiglion Fiorentino
Borgo Tranquilitta - La Luna
  • 5 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany villa for 5 in 2 bedrooms with shared pool in detatched cottage, 7km from Castiglion Fiorentino
Villa Sophia
  • 12 Sleeps
  • 6 Bedrooms
  • Pool
View Tuscany villa with 6 bedrooms and 6 bathrooms and private pool in Santa Margherita
Villa Francesca
  • 6 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany villa near Cortona, sleeps 6, with private pool ideal for Tuscany family holidays
Villa Maltilde
  • 4 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany villa for 4 in 2 bedrooms with private pool
Villa Nonna
  • 9 Sleeps
  • 4 Bedrooms
  • Pool
View Tuscany villa with 4 bedrooms and private pool close to Castiglion Fiorentino
Villa Coppa
  • 6 Sleeps
  • 3 Bedrooms
View Tuscany villa with 3 bedrooms, stunning views, close to Cortona
Casa Sophia di Brolio
  • 8 Sleeps
  • 4 Bedrooms
  • Pool
View Tuscany villa with 4 bedrooms, private pool and gardens
Borgo Tranquilitta - Le Stelle
  • 4 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany cottage for up to 4 with shared pool and private BBQ near Castiglion Fiorentino
Villa Irena
  • 10 Sleeps
  • 6 Bedrooms
  • Pool
View Tuscany villa with 6 bedrooms in the Val di Chio close to Castiglion Fiorentino, Arezzo
Villa Margarita
  • 13 Sleeps
  • 6 Bedrooms
  • Pool
View Tuscany villa with 6 bedrooms and private pool in the Val di Chio near Castiglion Fiorentino
Villa Castiglioni
  • 14 Sleeps
  • 6 Bedrooms
  • Pool
View 6 bedroom luxury Tuscany villa with pool and air conditioning, private grounds, near Castiglion Fiorentino
Villa Castello Roccolo
  • 6 Sleeps
  • 3 Bedrooms
  • Pool
View Tuscany villa with 3 bedrooms, sleeps 6, with stunning views on the Castiglion Fiorentino hillside, private pool
Casa Serena
  • 4 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany villa for 4 with private pool in the Val di Chio near Castiglion Fiorentino
Villa Grande
  • 6 Sleeps
  • 3 Bedrooms
  • Pool
View Tuscany villa for 6 in 3 bedrooms with private pool near Castiglion Fiorentino
Casa dei Sogni
  • 6 Sleeps
  • 3 Bedrooms
  • Pool
View Tuscany villa for 6 in 3 bedrooms with private pool and air conditioning
Villa Carla Tuscany
  • 6 Sleeps
  • 3 Bedrooms
  • Pool
View Beautiful and Spacious Tuscan Villa for 6; with 3 bedrooms, private pool overlooking the Tuscan hill town of Castiglion Fiorentino
Borgo Tranquilitta - Il Sole
  • 4 Sleeps
  • 2 Bedrooms
  • Pool
View Tuscany villa for 4 with 2 bedrooms and pool close to Castiglion Fiorentino and Val di Chio

Explore the charms of Tuscany. Tuscan Hilltowns, festivals, wineries, shops and restaurants

Tuscany Area Guide »

Castiglion Fiorentino & Cortona, Tuscany

Tuscany is the ideal destination for families and for those looking to experience the famous festivals and cultural activities of Italy. Our holiday cottages and villas are mainly around the areas of Castiglion Fiorentino and Cortona. Castiglion Fiorentino remains unspoilt. It is a bucolic, working rural area where the maintenance of vineyards, olive groves and vast fields of crops provide many of the local population their livelihood.

Visiting This part of Tuscany is about peace and tranquillity; about relaxing and unwinding.  However, many visitors want to get a flavour of Tuscan life and to visit the amazing  architectural and religious sites  -  and to explore the Tuscan countryside. For touring Tuscany,  a car is pretty much a necessity - although, in the town of Castiglion Fiorentino there are bike rentals along with many bike trails to explore the local area.

Another benefit of this part of Tuscany is its location. Castiglion Fiorentino has a train station with regular trains to Arezzo, Florence and Rome.  Florence is roughly a 1hr train\car journey and sets you down in the very heart of this magnificent city. In addition, easy day trips to the wine areas of Chianti, Montepulciano and Montalcino (Brunello) are easy -  as are day trips to the many beautiful Tuscan hill towns and villages. For guests looking for extra fun or pampering, there are many spa resorts including Rapolano Terme to enjoy.

Whilst you are here, we can help organise cooking classes, truffle hunting, scooter hire, etc., and if you need to hire a car, do check our car rental rates.

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Contact Us

For further assistance choosing a villa for your holiday in Tuscany, either send us an email, phone, or use the form on our contact page.

Email:

Telephone #1: +39 346 327 9144

Telehone #2 (solo SMS Italiano): +39 333 6406494

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